By M A McKervey, Chemical Society
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Extra resources for Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976
Ghatak, S. K. Alam, P. Chakraborti, and B. C. S. R. Wilson and K. A. Tanaka, M. Aoyagi, Chem. and Phmm. Bull. (Japan), 1976,24,782;M. H. Sherlock and N. 3947588 (Chem. , 1976,85,5382). S. S. Wulfman, R. S. MeDaniel, and B. W. , pp. 1241,1251. S. -H. B. Yen, J . Amer. Chem. SOL, 1976,98,297;J . Org. , 1976,41,1273. ' l 9 Rhodium(I1)carboxylates,and in particular the butanoate and pivalate which are readily soluble, have been found to be particularly useful catalysts in the diazoalkene cyclopropanation of olefins substituted at the double bond where palladium(1:) acetate and copper(1) triflate are frequently ineffective.
Delay, T. W. Wallace, and U. Burger, H e h . Chim. Acta, 1976, 59, 2355: C. W. Jefford, J. Mareda. -C. E. Gehret, nT. Kabengele, W. D. Graham, and U. Burger. J . Amer. Chem. , 197698, lob 2585. R. A. Moss and J. K. S. Chem. , 1976,950. lo' R . N. Haszeldine, C. R. Pool, A. E. Tipping, and R. O'B. S. Perkin I , 1976, 513. 'lo0. M. Nefedov, V. M. Shostakovskii, and M. I. Kravchenko, Izuest. Akad. , Ser. , 1976, lo' '11 379 (Chem. , 1976,85, 20973); V. L. P. 3969392 (Chem. , 1976,85, 123664). P. Prendergast and W.
J . , 1976,29, 1699. H. Prinzbach, V. Wessely, and H. Fritz,Tetrahedron Letters, 1976, 2765. G. Kaup and K. RBsch, Angew. Chem. Znternat. , 1976,15, 163; K. Menke and H. , p. 165; R. Nader and A. , p. 166. Thermal equilibration of (109) leads to (110) and the stable norcaradiene (1 11) which may also be a primary product of the cyclopropanation reaction. Although the details of the monocyclopropanation product of (106; R = C0,Me) are vague (a footnote in the communication), it would appear that the electron-withdrawing methoxy-carbonyl substituents make a significant contribution to the stability of the ‘norcaradieneophane’.